Dimethylene tartrate and method of making same.



UNITED STATES PATENT OFFICE.

WILHELM STERNBERG, OF BERLIN, GERMANY, ASSIGNOR TO CI-IEMISCHE FABRIKAUF AOTIEN, (VORM. E. SOHERINGQ OF BERLIN, GERMANY.

DIMETHYLENE TARTRATE AND METHOD OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 699,423, dated May 6,1902.

'Application filed October 29, 1901. Serial No. 80,450. (No spaciinensa)To aZZ whom it may concern:

Be it known that I, WILHELM STERNBERG, chemist, doctor of philosophy, asubject of the Emperor of Germany, residing at Berlin, Kingdom ofPrussia, German Empire, have invented a new and useful Improvement inDimethylene Tartrate and Method of Making the Same, of which thefollowing is a specification.

My invention relates to the manufacture of the hitherto-unknowndimethylene tartrate, (dimethylene ester of tartaric acid,) which is ofuse in medicine.

Tollens (see Liebigs Annalcn, 292, pages 53 and 54) tried to condensetartaric acid with formic aldehyde, using hydrochloric acid. He did not,however, make the compound hereinafter described.

If in place of hydrochloric acid other agents of condensation be used,which at the same time withdraw Water'such as sulfuric acid orphosphorous pentoxid and the like-the dimethylene ester of tartaric acidis produced, which has nothing in common with the problematical bodydescribed by Tollens.

Methylene tartrate is useful for the disinfection of the urinarypassages and is preferably administered in doses of about 0.1 to 0.25grams three times daily.

To manufacture the compound, one proceeds, for example, as follows:Seven kilograms of tartaric acid are heated with three kilograms ofpolymeric formaldehyde (paraformaldehyde, trioxymethylene) or thecorresponding quantity of a forty-per-cent. solution of formic aldehydeto from 140 to 150 centigrade until a clear solution is produced.

The product of reaction is mixed when at about 60 centigrade withfifteen kilograms of sulfuric acid. As heat is evolved it is preferable,in order to prevent a possible carboniagents of condensation-such as,for example,

phosphorous pentoXid-may be employed.

Dimethylene tartrate forms fine needles, which melt at 120 centigradewithout decomposition. It is easily soluble in warm water, withdecomposition, however, formic aldehyde being split off. It is easilysoluble in alcohol, acetone, and chloroform and can be crystallized outof the same. It is unstable at the blood temperature in the presence ofa weak solution of soda. It is even more un stable in the presence ofcaustic alkalies. On the other hand, it is more stable in the presenceof acids.

I claim as my invention 1. The herein-described process of manufacturingdimethylene tartrate, which consists in causing formaldehyde to reactupon tartaric acid in the presence of a condensing agent which at thesame time withdraws water, and isolating the resulting product,substantially as set forth;

2. As a new product the herein-described dimethylene tartrate formingfine needles which melt at 120 centigrade, being easily soluble inalcohol, acetone and chloroform,

substantially as set forth.

In testimony whereof I have signed my name to this specification in thepresence of two subscribing witnesses.

VILHELM STERNBERG.

\Vitnesses:

WOLDEMAR I-IAUPT, HENRY HASPER.

